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RE: Rewards
While good in theory, I think the point is to provide bad teams with a chance to rebuild while not crippling teams that had success. The pre-season FA draft is a random order (if I understand correctly), so that keeps it fair to all teams. The rookie draft is weighted toward teams with lower winning percentages.
As for the "economics" of real baseball, the Cubbies seem to have always drawn well win-or-lose. Other teams, like the Expos, can't draw flies even when times are good. The Yankees are nearly cover their player salaries with just their television contract, so ticket sales are just a bonus. So winning does not necessarily equate to having a sound economic base for a franchise.
A good argument you propose, but I think we're forgetting about the 'game' aspect here. You've got to give all owners a chance to compete. Otherwise, nobody would ever take on a down-trodden franchise. There would be a long wait to be competitive unless you sold out the current day to get tons of picks. And isn't is a lot more fun to own Jeromy Burnitz than 2 nameless #1 picks???
~ Bill